Molecular Design and Synthesis, Department of Chemistry, KU Leuven , Celestijnenlaan 200F, 3001 Leuven, Belgium.
Org Lett. 2013 Jun 21;15(12):2910-3. doi: 10.1021/ol400825w. Epub 2013 Jun 4.
The synthesis of [9]- and [11]thiahelicenes, as well as the preparation of lower homologues such as [5]-, [6]-, and [7]thiahelicenes is reported. Efficient palladium catalyzed coupling reactions were employed. Triorganoindium derivatives were selectively mono-cross-coupled with N-methyl-3,4-dibromomaleimide followed by Stille coupling with the readily available building block naphthodithiophene. Oxidative photocyclization of the conjugated precursors using visible light was employed to synthesize a series of thia[n]helicenes. This modular synthetic methodology is independent of the length of the helical backbone.
本文报道了[9]-和[11]噻吩并螺旋芳烃以及较低同系物如[5]-, [6]-, 和[7]噻吩并螺旋芳烃的合成方法。该方法采用高效钯催化偶联反应。三芳基铟衍生物选择性地与 N-甲基-3,4-二溴马来酰亚胺单交叉偶联，然后与易得的构筑块萘并二噻吩进行 Stille 偶联。使用可见光对共轭前体进行氧化光环化，合成了一系列噻吩并[n]螺旋芳烃。这种模块化的合成方法与螺旋主链的长度无关。
